Azodyestuff



P atent ecl AugQS i931; r

.Paul Zervas,

Cologne-Mulheim, and Heinrich Clingestein, Cologne-on-the-Rhine, Germany,

assignors to General Aniline WVorkgIna, New

York, N; Y., a Corporation of Delaware "No Drawing. Application August 6, 1932, Serial 7 Ne. 627,810, and in Germany'September 10,

The present invention'relates to new azodyestuffs, more particularly it"relates to dyestuffs which may be represented by the probable general formula: we

5 o x 1 UR wherein R stands for a radical of ,thebenzene series, forexample, for. a benzene nucleus which maybe substituted by halogen, .alkyl, alkoxy or a nitro group, R stands for alkyl, aralkyl or aryl,

5 for example; for methyl, ethyl orbenzyl, in which the nucleus maybe substitutedior example-by halogen, methyl, ethyl, :methoxy; ethoxy, or for a benzene nucleus which may bel-substitute'dfor example, by halogen, methyl; ethyhmethoxy and ethoxy, R" standsforhydrogen', alkyl, :aralkyl or aryl, for example, for methyl, ethyl -or'benzyl, in

which the nucleus may be substituted for example .Ouronew dyestuffs are obtainable by-diazotizing ,a primary aminel of the behzenesriesfand 5 coupling in alkaline solution with a coupling 5 component, of the general formula:

wherein R, R", alk and n mean the same as stated above. r Y

The coupling components used in our invention 551:.are obtainable, for example, by the action of amnaphthalene-4.6-disulfonic acid; Themoniaor iprimaryialkyle, aralkylor arylamines upon; a1kyl-, iaralkyl- .1012 oarylsulfonic acid ch10:

rides, condensationfwith a halogen fatty acid, I

I transformingjthe halogen. fatty acid-derivative into the corresponding acid chloride according to known. methods, andjfinallyf condensing the acid chloride with an, aminonaphtholsulfonic acid.

J Our new dyestufjs are; in form of their alk ali met salts en r l y ar f f d s dyein w'oolfrom an acid bath-generally red "shades'of good fastness to fullingand light, I

The invention is illustrated by the followi examples without being limited thereto:

' xample, 1'."I o'a soda alkaline solution of 53 parts' by weight of p-toluenesulfaminoacetyl- 1 amino-8-hydroxynaphthalene 3.G-disulfonic acid there is added a diazobenzene solution of 9,3

" parts by Weight of aniline.) The isolated dyestuff dyes wool red shades; in its free-state it has the following formula: i 1

SOaH

A dyestufl having'similar properties, but dye- 7 ing somewhat more yellowish red is obtained by substituting the aniline, by 12,75 parts by weight ofD-chloroaniline; q T' Example 2. A dia'zobenzene solution of .9,3

partsrby weight of aniline'isaddedto'a soda alka'-:. line solut-ionof 54,4 parts by weight-"of p'i-toluenesulfid .N -methylaminoacetyl laminO-B-hydrO ythus isolate'd dyes w'oolre'd shades of good fast nessto fullin'gQ In its free ste red the following formula:

. I 035 on i wg-oo-om-N I A dyestuff having similar properties is obtained when substituting the p-toluenesulfo-N-methylaminoacetyl 1 amino 3 hydroxyna phthalene 4.6-disu1fonic acid by 55,8 parts by weight of bog-Oo loo parts by Weight p toluenesulfo N ethylaminoacetyl- 1 amino-8- hydroxynaphthalene-LG-disulfonic acid.

Example 3.-A diazotoluene solution of 10,7 of =o-toluidine is coupled with a soda alkaline solution of 46,4 parts by weight of p-toluenesulfo N methylaminoacetyl -2- amino 8 hydroxynaphthalene 6 sulfonic acid. The

dyestufi thus obtained dyes wool red shades of good fastness to fulling. In its free state it has the following formula:

Dyestuffs having similar properties are obtained when replacing the o-toluidine by 12,3

scan

Dyestuffs having similar properties are obtained when replacing the methanesulfo-N- methylaminoacetyl-l-amino-B-hydroxynaphthalene-4.6-disulfonic acid by 48,2 parts by weight of methanesulfo-N-methylamino propionyl-1- amino-8ehydroxynaphthalene-4.6-disulfonic acid,

or by 54,4 parts by weight of -benzylsulfo-N-. methylaminoacetyl-1-amino 8-hydroxynaphtha- 118116-45-d1sl11f0n10 acid.

We claim: 1. As new products azodyestuffs of the probable general formula:

sorOoEn wherein R stands for a radical of the benzene series, B. stands for alkyl, aralkyl or aryl, R" stands for hydrogen, alkyl, aralkyl or aryl, alk? stands for an alkylene group, n stands for one of the numbers one and two,-th e azo bridge being attached to the naphthalene nucleus in o-position to the hydroxy group, being in form of their alkali metal salts generally dark red powders, dyeing wool generally red shades of good fastness to fulling and light.

2. As new products azodyestufis of the probable general formula: V

wherein R stands for a benzene nucleus which may be substituted by substituents selected from the group consisting of halogen, alkyl, alkoxy and the nitro group, R stands for methyl, ethyl or a radical of the benzene series, R" stands for hydrogen, methyl, ethyl or a radical of the benzyl series, alk stands for a methylene or ethylene group, n stands for one of the numbers one and two, the azobridge being attached to the naphthalene nucleus in o-position to the hydroxy group, being in form of their alkali metal salts generally dark red powders, dyeing wool generally red shades'of good fastness to fulling and light.

3. As a new product the azodyestufi of the following formula:

being inform of its alkali metal salts a dark red powder, dyeing wool red shades of good fastness properties. v 1 V b g 4. As a new product the azodyestuff of the fol 130 lowing formula:

being in form of its alkali metal salts a dark red powder, dyeing wool red shades of good fastness 

